data_mo_ch_tsk_1_300k_0m_a
_audit_creation_date               2025-02-25
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number       '2014/7'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           '0.5(H4 O2), C26 H12 F6 N4'
_chemical_formula_sum              'C26 H14 F6 N4 O'
_chemical_formula_weight           512.41
_chemical_melting_point            ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'orthorhombic'
_space_group_IT_number             52
_space_group_name_H-M_alt          'P n n a'
_space_group_name_Hall             '-P 2a 2bc'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 'x, -y+1/2, -z+1/2'
 '-x+1/2, y+1/2, -z+1/2'
 '-x+1/2, -y, z'
 '-x, -y, -z'
 '-x, y-1/2, z-1/2'
 'x-1/2, -y-1/2, z-1/2'
 'x-1/2, y, -z'

_cell_length_a                     9.9295(15)
_cell_length_b                     12.7666(17)
_cell_length_c                     17.765(3)
_cell_angle_alpha                  90
_cell_angle_beta                   90
_cell_angle_gamma                  90
_cell_volume                       2252.0(6)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      5165
_cell_measurement_temperature      330.0
_cell_measurement_theta_max        25.276
_cell_measurement_theta_min        2.293
_shelx_estimated_absorpt_T_max     0.980
_shelx_estimated_absorpt_T_min     0.957
_exptl_absorpt_coefficient_mu      0.129
_exptl_absorpt_correction_T_max    0.7456
_exptl_absorpt_correction_T_min    0.6838
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0762 before and 0.0614 after correction.
The Ratio of minimum to maximum transmission is 0.9171.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              'clear yellowish yellow'
_exptl_crystal_colour_lustre       clear
_exptl_crystal_colour_modifier     yellowish
_exptl_crystal_colour_primary      yellow
_exptl_crystal_density_diffrn      1.511
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               1040
_exptl_crystal_size_max            0.34
_exptl_crystal_size_mid            0.21
_exptl_crystal_size_min            0.156
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0634
_diffrn_reflns_av_unetI/netI       0.0238
_diffrn_reflns_Laue_measured_fraction_full  0.995
_diffrn_reflns_Laue_measured_fraction_max  0.995
_diffrn_reflns_limit_h_max         11
_diffrn_reflns_limit_h_min         -11
_diffrn_reflns_limit_k_max         13
_diffrn_reflns_limit_k_min         -15
_diffrn_reflns_limit_l_max         21
_diffrn_reflns_limit_l_min         -21
_diffrn_reflns_number              29702
_diffrn_reflns_point_group_measured_fraction_full  0.995
_diffrn_reflns_point_group_measured_fraction_max  0.995
_diffrn_reflns_theta_full          24.996
_diffrn_reflns_theta_max           24.996
_diffrn_reflns_theta_min           1.964
_diffrn_ambient_temperature        330.0
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.995
_diffrn_measured_fraction_theta_max  0.995
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     ?
_diffrn_source_current             1.4
_diffrn_source_power               0.07
_diffrn_source_voltage             50.0
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  1428
_reflns_number_total               1978
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'SAINT V8.40B (?, 2016)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics      'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution      'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max           0.158
_refine_diff_density_min           -0.212
_refine_diff_density_rms           0.034
_refine_ls_extinction_coef         0.0042(8)
_refine_ls_extinction_expression  
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_extinction_method       'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref     1.054
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       202
_refine_ls_number_reflns           1978
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0694
_refine_ls_R_factor_gt             0.0488
_refine_ls_restrained_S_all        1.054
_refine_ls_shift/su_max            0.001
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0513P)²+1.1840P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1218
_refine_ls_wR_factor_ref           0.1420
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Others
 Sof(F6A)=1-FVAR(1)
 Sof(F6)=FVAR(1)
 Sof(F1A)=1-FVAR(2)
 Sof(F1)=FVAR(2)
 Sof(F2A)=1-FVAR(3)
 Sof(F2)=FVAR(3)
 Fixed Sof: H00A(0.5) H00B(0.5)
3.a Free rotating group:
 O001(H00A,H00B)
3.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C9(H9), C10(H10), C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 O001 O 0.7500 0.5000 0.55396(14) 0.0725(7) Uani 1 2 d GS T P . .
 H00A H 0.7176 0.5466 0.5250 0.109 Uiso 0.5 1 d G U P . .
 H00B H 0.7526 0.4449 0.5271 0.109 Uiso 0.5 1 d G U P . .
 F2 F 1.0228(15) 0.3675(3) 0.1069(4) 0.141(5) Uani 0.64(2) 1 d . . P A 1
 C6 C 0.8192(2) 0.37740(15) 0.22301(14) 0.0525(6) Uani 1 1 d . . . . .
 H6 H 0.7670 0.3615 0.1811 0.063 Uiso 1 1 calc R U . . .
 N2 N 0.65771(19) 0.30956(13) 0.32266(9) 0.0506(5) Uani 1 1 d . . . . .
 F1 F 1.1121(9) 0.5001(10) 0.1454(5) 0.203(4) Uani 0.621(14) 1 d . . P A 1
 C2 C 0.9935(4) 0.4494(3) 0.1392(3) 0.1055(14) Uani 1 1 d . . . . .
 C3 C 0.9439(2) 0.42516(17) 0.2158(2) 0.0742(8) Uani 1 1 d . . . . .
 C4 C 0.7757(2) 0.35447(15) 0.29465(13) 0.0501(6) Uani 1 1 d . . . . .
 C5 C 0.5437(2) 0.26966(16) 0.28673(12) 0.0502(5) Uani 1 1 d . . . . .
 F6 F 0.9147(12) 0.5034(17) 0.1054(7) 0.167(7) Uani 0.54(2) 1 d . . P A 1
 C7 C 0.4222(3) 0.27104(19) 0.32739(18) 0.0746(8) Uani 1 1 d . . . . .
 C8 C 0.3022(3) 0.2560(3) 0.28772(19) 0.1035(14) Uani 1 1 d . . . . .
 H8 H 0.2210 0.2544 0.3138 0.124 Uiso 1 1 calc R U . . .
 C9 C 0.4299(5) 0.2842(3) 0.4074(2) 0.1083(14) Uani 1 1 d . . . . .
 H9 H 0.3510 0.2804 0.4355 0.130 Uiso 1 1 calc R U . . .
 C10 C 0.5447(5) 0.3016(3) 0.44281(19) 0.1118(15) Uani 1 1 d . . . . .
 H10 H 0.5475 0.3004 0.4951 0.134 Uiso 1 1 calc R U . . .
 C11 C 0.6638(4) 0.32194(19) 0.40099(14) 0.0754(8) Uani 1 1 d . . . . .
 N1 N 0.7787(3) 0.36194(18) 0.42389(14) 0.0944(9) Uani 1 1 d . . . . .
 C13 C 0.8493(3) 0.38329(18) 0.35892(17) 0.0747(8) Uani 1 1 d . . . . .
 C14 C 0.9752(4) 0.4318(2) 0.3497(3) 0.1076(15) Uani 1 1 d . . . . .
 H14 H 1.0269 0.4503 0.3913 0.129 Uiso 1 1 calc R U . . .
 C15 C 1.0198(3) 0.4510(2) 0.2791(3) 0.1053(14) Uani 1 1 d . . . . .
 H15 H 1.1035 0.4825 0.2726 0.126 Uiso 1 1 calc R U . . .
 F6A F 0.978(3) 0.5443(5) 0.1145(7) 0.187(8) Uani 0.46(2) 1 d . . P A 2
 F1A F 0.9134(15) 0.4048(13) 0.0753(4) 0.128(5) Uani 0.379(14) 1 d . . P A 2
 F2A F 1.1103(16) 0.416(2) 0.1174(10) 0.183(11) Uani 0.36(2) 1 d . . P A 2


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 O001 H00A 0.8499 . ?
 O001 H00B 0.8500 . ?
 F2 C2 1.228(6) . ?
 C6 H6 0.9300 . ?
 C6 C3 1.386(3) . ?
 C6 C4 1.376(3) . ?
 N2 C4 1.396(3) . ?
 N2 C5 1.396(3) . ?
 N2 C11 1.402(3) . ?
 F1 C2 1.349(6) . ?
 C2 C3 1.479(5) . ?
 C2 F6 1.204(7) . ?
 C2 F6A 1.298(9) . ?
 C2 F1A 1.499(9) . ?
 C2 F2A 1.293(8) . ?
 C3 C15 1.394(5) . ?
 C4 C13 1.405(3) . ?
 C5 C5 1.398(4) 2 ?
 C5 C7 1.406(3) . ?
 C7 C8 1.398(4) . ?
 C7 C9 1.433(5) . ?
 C8 C8 1.349(7) 2 ?
 C8 H8 0.9300 . ?
 C9 H9 0.9300 . ?
 C9 C10 1.320(5) . ?
 C10 H10 0.9300 . ?
 C10 C11 1.421(5) . ?
 C11 N1 1.315(4) . ?
 N1 C13 1.378(4) . ?
 C13 C14 1.405(5) . ?
 C14 H14 0.9300 . ?
 C14 C15 1.353(5) . ?
 C15 H15 0.9300 . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 H00A O001 H00B 104.5 . . ?
 C3 C6 H6 121.3 . . ?
 C4 C6 H6 121.3 . . ?
 C4 C6 C3 117.4(2) . . ?
 C4 N2 C11 105.8(2) . . ?
 C5 N2 C4 131.87(18) . . ?
 C5 N2 C11 122.0(2) . . ?
 F2 C2 F1 103.9(8) . . ?
 F2 C2 C3 109.4(4) . . ?
 F1 C2 C3 108.5(5) . . ?
 C3 C2 F1A 116.1(3) . . ?
 F6 C2 F2 114.1(12) . . ?
 F6 C2 F1 109.4(11) . . ?
 F6 C2 C3 111.2(4) . . ?
 F6A C2 C3 117.9(7) . . ?
 F6A C2 F1A 92.1(9) . . ?
 F2A C2 C3 120.4(6) . . ?
 F2A C2 F6A 107.8(14) . . ?
 F2A C2 F1A 97.2(13) . . ?
 C6 C3 C2 118.4(3) . . ?
 C6 C3 C15 120.8(3) . . ?
 C15 C3 C2 120.8(3) . . ?
 C6 C4 N2 132.90(19) . . ?
 C6 C4 C13 122.2(2) . . ?
 N2 C4 C13 104.8(2) . . ?
 N2 C5 C5 123.91(12) . 2 ?
 N2 C5 C7 117.1(2) . . ?
 C5 C5 C7 118.94(17) 2 . ?
 C5 C7 C9 117.7(3) . . ?
 C8 C7 C5 118.1(3) . . ?
 C8 C7 C9 124.2(3) . . ?
 C7 C8 H8 119.4 . . ?
 C8 C8 C7 121.11(17) 2 . ?
 C8 C8 H8 119.4 2 . ?
 C7 C9 H9 118.7 . . ?
 C10 C9 C7 122.6(3) . . ?
 C10 C9 H9 118.7 . . ?
 C9 C10 H10 120.0 . . ?
 C9 C10 C11 120.0(3) . . ?
 C11 C10 H10 120.0 . . ?
 N2 C11 C10 117.6(3) . . ?
 N1 C11 N2 112.8(3) . . ?
 N1 C11 C10 129.2(3) . . ?
 C11 N1 C13 105.0(2) . . ?
 N1 C13 C4 111.4(3) . . ?
 N1 C13 C14 129.6(3) . . ?
 C14 C13 C4 119.0(3) . . ?
 C13 C14 H14 120.7 . . ?
 C15 C14 C13 118.6(3) . . ?
 C15 C14 H14 120.7 . . ?
 C3 C15 H15 119.0 . . ?
 C14 C15 C3 121.9(3) . . ?
 C14 C15 H15 119.0 . . ?

loop_
  _geom_torsion_atom_site_label_1
  _geom_torsion_atom_site_label_2
  _geom_torsion_atom_site_label_3
  _geom_torsion_atom_site_label_4
  _geom_torsion
  _geom_torsion_site_symmetry_1
  _geom_torsion_site_symmetry_2
  _geom_torsion_site_symmetry_3
  _geom_torsion_site_symmetry_4
  _geom_torsion_publ_flag
 F2 C2 C3 C6 -70.5(8) . . . . ?
 F2 C2 C3 C15 110.3(8) . . . . ?
 C6 C3 C15 C14 -0.6(4) . . . . ?
 C6 C4 C13 N1 173.5(2) . . . . ?
 C6 C4 C13 C14 -3.7(3) . . . . ?
 N2 C4 C13 N1 -2.6(2) . . . . ?
 N2 C4 C13 C14 -179.8(2) . . . . ?
 N2 C5 C7 C8 164.7(2) . . . . ?
 N2 C5 C7 C9 -17.4(3) . . . . ?
 N2 C11 N1 C13 3.7(3) . . . . ?
 F1 C2 C3 C6 176.8(7) . . . . ?
 F1 C2 C3 C15 -2.3(8) . . . . ?
 C2 C3 C15 C14 178.5(3) . . . . ?
 C3 C6 C4 N2 178.6(2) . . . . ?
 C3 C6 C4 C13 3.8(3) . . . . ?
 C4 C6 C3 C2 179.2(2) . . . . ?
 C4 C6 C3 C15 -1.6(3) . . . . ?
 C4 N2 C5 C5 25.5(4) . . . 2 ?
 C4 N2 C5 C7 -153.6(2) . . . . ?
 C4 N2 C11 C10 168.0(2) . . . . ?
 C4 N2 C11 N1 -5.4(3) . . . . ?
 C4 C13 C14 C15 1.4(4) . . . . ?
 C5 N2 C4 C6 2.0(4) . . . . ?
 C5 N2 C4 C13 177.41(19) . . . . ?
 C5 N2 C11 C10 -5.7(3) . . . . ?
 C5 N2 C11 N1 -179.13(19) . . . . ?
 C5 C5 C7 C8 -14.5(4) 2 . . . ?
 C5 C5 C7 C9 163.5(3) 2 . . . ?
 C5 C7 C8 C8 -2.1(5) . . . 2 ?
 C5 C7 C9 C10 4.4(5) . . . . ?
 F6 C2 C3 C6 56.4(14) . . . . ?
 F6 C2 C3 C15 -122.7(14) . . . . ?
 C7 C9 C10 C11 8.6(5) . . . . ?
 C8 C7 C9 C10 -177.8(3) . . . . ?
 C9 C7 C8 C8 -179.9(4) . . . 2 ?
 C9 C10 C11 N2 -8.0(4) . . . . ?
 C9 C10 C11 N1 164.2(3) . . . . ?
 C10 C11 N1 C13 -168.7(3) . . . . ?
 C11 N2 C4 C6 -170.9(2) . . . . ?
 C11 N2 C4 C13 4.5(2) . . . . ?
 C11 N2 C5 C5 -162.5(2) . . . 2 ?
 C11 N2 C5 C7 18.3(3) . . . . ?
 C11 N1 C13 C4 -0.6(3) . . . . ?
 C11 N1 C13 C14 176.2(3) . . . . ?
 N1 C13 C14 C15 -175.2(3) . . . . ?
 C13 C14 C15 C3 0.6(5) . . . . ?
 F6A C2 C3 C6 98.7(14) . . . . ?
 F6A C2 C3 C15 -80.5(14) . . . . ?
 F1A C2 C3 C6 -9.1(10) . . . . ?
 F1A C2 C3 C15 171.7(9) . . . . ?
 F2A C2 C3 C6 -126.0(18) . . . . ?
 F2A C2 C3 C15 54.9(18) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'
